
TY  - JOUR
A1  - Lap, BV 
A1  - Williams, LR 
T1  - Cyclic analogues of &#946;-adrenergic blocking agents <I>cis</I>- and <I>trans</I>-3-Amino-6-bromochroman-4-ols
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1976
VL  - 29
IS  - 8
SP  - 1791
EP  - 1799
KW  - 
UR  - https://doi.org/10.1071/CH9761791 
N2  - N-(6-Bromo-4-oxochroman-3-yl)acetamide (4; R = Ac) can be reduced by sodium borohydride to the cis-N-(6-bromo-4-hydroxychroman-3-yl)acetamide (6) and this can be hydrolysed to give the cis-3-amino-6-bromochroman-4-ol (7) or converted into the corresponding trans-3-amino-6-bromo- chroman-4-ol (12) by chlorination with inversion followed by hydrolysis of the chloride (8) to the alcohol with retention of configuration. The assignment of configuration of the 3,4-substituted chromans is based on the value of the coupling constants between the H3 proton and the methylene protons on C2 and is supported by an observed difference in the rate of hydrolysis of the two N-(6-bromo-4-chlorochroman-3-yl)acetamides. 
ER  -

